GB1588517A - Preparation of m-aryloxybenzyl chloride and m-aryloxybenzal chloride - Google Patents
Preparation of m-aryloxybenzyl chloride and m-aryloxybenzal chloride Download PDFInfo
- Publication number
- GB1588517A GB1588517A GB41526/76A GB4152676A GB1588517A GB 1588517 A GB1588517 A GB 1588517A GB 41526/76 A GB41526/76 A GB 41526/76A GB 4152676 A GB4152676 A GB 4152676A GB 1588517 A GB1588517 A GB 1588517A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloride
- process according
- meta
- aryloxybenzal
- aryloxybenzyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 18
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims abstract description 10
- 239000003999 initiator Substances 0.000 claims abstract description 6
- UDONPJKEOAWFGI-UHFFFAOYSA-N 1-methyl-3-phenoxybenzene Chemical compound CC1=CC=CC(OC=2C=CC=CC=2)=C1 UDONPJKEOAWFGI-UHFFFAOYSA-N 0.000 claims abstract description 5
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 238000005660 chlorination reaction Methods 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- -1 peroxy compound Chemical class 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229950005499 carbon tetrachloride Drugs 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000012084 conversion product Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- JOVSDWRNVGOQNK-UHFFFAOYSA-N 1-(dichloromethyl)-3-phenoxybenzene Chemical compound ClC(Cl)C1=CC=CC(OC=2C=CC=CC=2)=C1 JOVSDWRNVGOQNK-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- QUYVTGFWFHQVRO-UHFFFAOYSA-N 1-(chloromethyl)-3-phenoxybenzene Chemical compound ClCC1=CC=CC(OC=2C=CC=CC=2)=C1 QUYVTGFWFHQVRO-UHFFFAOYSA-N 0.000 description 1
- 101100188555 Arabidopsis thaliana OCT6 gene Proteins 0.000 description 1
- 241001620634 Roger Species 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- CSKKAINPUYTTRW-UHFFFAOYSA-N tetradecoxycarbonyloxy tetradecyl carbonate Chemical compound CCCCCCCCCCCCCCOC(=O)OOC(=O)OCCCCCCCCCCCCCC CSKKAINPUYTTRW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for the preparation of a mixture of a meta-phenoxybenzyl chloride and a meta-phenoxybenzal chloride, which comprises chlorinating a meta-phenoxytoluene with sulphuryl chloride in the presence of a free-radical initiator under conditions such that the formation of ring-chlorinated derivatives is minimized.
Description
PATENT SPECIFICATION ( 11) 1 588 517
I ( 21) Application No 41526/76 ( 22) Filed 6 Oct 1976 ( 19) tn ( 23) Complete Specification Filed 4 Oct 1977 ( 44) Complete Specification Published 23 Apr 1981
0 ( 51) INT CL 3 C 07 C 43/225 ( 52) Index at Acceptance C 2 C 220 227 22 Y 313 31 Y 339 364 36 Y 38 Y 43 X 440 624 699 FJ WR I ( 72) Inventors: ROGER ARTHUR SHELDON ROBERT VAN HELDEN ( 54) PREPARATION OF M-ARYLOXYBENZYL CHLORIDE AND M-ARYLOXYBENZAL CHLORIDE ( 71) We, SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B V, a company organised under the laws of The Netherlands, of 30 Carel van Bylandtlaan, The Hague, The Netherlands, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement: 5
This invention relates to a process for the preparation of a mixture of a metaaryloxybenzyl chloride and a meta-aryloxybenzal chloride by the chlorination of the corresponding meta-aryloxytoluene.
Such mixtures of chlorides may be converted into metaaryloxybenzaldehydes which are valuable intermediates for the preparation of insecticidally-active esters 10 The direct chlorination of a meta-aryloxytoluene is complicated by the fact that in addition to substitution of the methyl group, introduction of chlorine atoms into one or both of the two aryl groups may take place.
The present invention is concerned with a chlorination process which avoids this problem is Accordingly the invention provides a process for the preparation of a mixture of a meta-aryloxybenzyl chloride and a meta-aryloxybenzal chloride, which comprises chlorinating a meta-aryloxytoluene with sulphuryl chloride in the presence of a free-radical initiator under conditions, wherein a relatively low concentration of sulphuryl chloride is maintained such that the formation of ring-chlorinated derivatives is minimised 20 Preferably a molar excess of the sulphuryl chloride is used, for example a 50-200 % molar excess may be used It has been found that an important factor influencing the formation of ring-chlorinated products is the concentration of the sulphuryl chloride In particular high initial concentration of SO 2 C 12 appear to favour ring subsitution It is therefore important to maintain a relatively low concentration of SO 2 C 12 during the reaction This may be 25 achieved conveniently by gradually adding the sulphuryl chloride to the reaction mixture, for example, over a period of 1 to 5 hours.
It is also preferred to carry out the reaction in a liquid diluent, for example a chlorinated hydrocarbon such as carbon tetra-chloride The chlorination is preferably effected at a temperature of 500 to 100 C, for example, by refluxing the reactants in a diluent having a 30 boiling point within this range The reaction may be conveniently carried out at atmospheric pressure.
The chlorination reaction is accompanied by the formation of hydrogen chloride which may lead to the occurrence of undesirable side-reactions, for example, the cleavage of the ether linkage in the starting material and/or products It is therefore preferred to remove HCI formed during the reaction, for example, by stripping with an inert gas such as nitrogen.
The free-radical initiator used in the reaction may be any of the compounds commonly used for the generation of free radicals, in particular azo and peroxycompounds, for example, azoisobutyranitrile, benzoyl peroxide, tertiary-butyl perbenzoate, or a peroxydicarbonate 40 1 588 517 such as dimyristylperoxydicarbonate.
The invention is illustrated further in the following Examples by reference to the preparation of a preferred mixture of 3-phenoxybenzyl chloride and 3phenoxybenzal chloride.
5 Examples I to III A solution of 3-phenoxytoluene (l Og) and azoisobutyronitrile ( 0 25 g) in carbon tetrachloride ( 50 ml) was heated under reflux while 50 ml of a solution of sulphuryl chloride in carbon tetrachloride was added dropwise at a rate of 14 ml per hour Refluxing was continued to give a total reaction time of 8 hours (Example I) or 5 hours (Examples II and 10 III) In Examples I and II a slow stream of nitrogen was passed through the mixture during the reaction The reaction product was examined by GLC; the results are given in the following Table.
TABLE I 15
Example SO 2 C 12 Conversion Product Composition equiv/mol 3-POT (%) R-CH 2 Cl R-CHC 12 ring-Cl Rest 3-POT 20 I 1 5 91 77 5 19 2 0 4 2 9 II 2 0 97 62 3 35 3 0 8 1 6 III 2 5 98 56 5 35 3 0 3 7 9 3-POT = 3-phenoxytoluene 25 R-CH 2 Cl = -3-phenoxybenzyl chloride R-CHC 12 = 3-phenoxybenzal chloride includes decomposition products from initiator.
30 Examples IV and V The procedure of Examples I to III was repeated except that all the sulphuryl chloride was added to the reaction mixture at the beginning of the reaction rather than dropwise during the course of the reaction The reaction time in both Examples IV and V was five hours and a nitrogen purge was employed in Example IV The results are summarised in 35 Table 2.
TABLE 2
Example 502 C 12 Conversion Product Composition 40 equiv/mol 3-POT (%) R-CH 2 CI R-CHC 12 ring-Cl Rest 3-POT IV 2 5 100 43 5 42 0 10 5 1 6 V 2 5 100 52 3 32 4 13 1 2 4 45 It will be seen from the results that whilst conversion of the 3-phenoxytoluene is complete there is a larger proportion of ring-chlorinated material present in the final 50product 50 Examples VI and VII The procedure of Examples I to III was repeated except that benzoyl peroxide was employed as catalyst The reaction time was 6 hours and a nitrogen purge was employed.
The results are shown in Table 3.
1 588 517 TABLE 3
Example SO 2 C 12 Conversion Product Conversion equiv/mol 3-POT (%) R-CH 2 Cl R-CHC 12 ring-Cl Rest 3-POT 5 VI 1 5 88 68 2 29 6 2 2 VII 2 0 98 56 9 40 8 2 3
Claims (11)
1 A process for the preparation of a mixture of a meta-aryloxybenzyl chloride and a meta-aryloxybenzal chloride, which comprises chlorinating a metaaryloxytoluene with sulphuryl chloride in the presence of a free-radical initiator under conditions wherein a relatively low concentration of sulphuryl chloride is maintained such that the formation of ring-chlorinated derivatives is minimised 15
2 A process according to claim 1 wherein a molar excess in the range 50200 % of sulphuryl chloride is used.
3 A process according claim 1 or 2 wherein the sulphuryl chloride is added to the reaction mixture over a period of 1-5 hours.
4 A process according to any one of the preceding claims which is carried out in a 20 chlorinated hydrocarbon.
A process according to any one of the preceding claims wherein chlorination is effected at a temperature in the range 50-100 C.
6 A process according to any one of the preceding claims wherein hydrogen chloride formed during the chlorination is removed during the reaction 25
7 A process according to any one of the preceding claims wherein the free radical initiator is an azo or peroxy compound.
8 A process according to any one of the preceding claims wherein the metaaryloxytoluene is 3-phenoxytoluene.
9 A process according to claim 1 substantially as hereinbefore described and with 30 reference to any one of Examples I to III.
A process according to claim 1 substantially as hereinbefore described and with reference to Example VI or VII.
11 A mixture of meta-aryloxybenzyl chloride and meta-aryloxybenzal chloride prepared according to the process claimed in any one of the preceding claims 35 R C ROGERS, Chartered Patent Agent, Shell Centre, London, SE 1 7 NA 40 Agent for the Applicant.
Printed for Her Majesty's Stationery Office, by Croydon Printing Company Limited, Croydon Surrey, 1981.
Published by The Patent Office, 25 Southampton Buildings, London, WC 2 A l AY, from which copies may be obtained.
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB41526/76A GB1588517A (en) | 1976-10-06 | 1976-10-06 | Preparation of m-aryloxybenzyl chloride and m-aryloxybenzal chloride |
| CA285,840A CA1104159A (en) | 1976-10-06 | 1977-08-31 | Chlorination of meta-phenoxytoluene |
| US05/836,807 US4146737A (en) | 1976-10-06 | 1977-09-26 | Chlorination of 3-phenoxytoluene |
| BR7706612A BR7706612A (en) | 1976-10-06 | 1977-10-04 | MIXING A META-ARYLOXY-BENZILINE CHLORIDE AND A META-ARYLOXYBENZAL CHLORIDE AND PROCESS FOR PREPARING THE SAME |
| MX776450U MX5162E (en) | 1976-10-06 | 1977-10-04 | PROCEDURE FOR PREPARING A MIXTURE OF META-ARYLOXYBENZYL CHLORIDE AND META-ARYLOXYZENZAL CHLORIDE |
| DE2744603A DE2744603C2 (en) | 1976-10-06 | 1977-10-04 | Process for the preparation of a mixture of m-aryloxybenzyl chloride and m-aryloxybenzal chloride |
| CH1213377A CH630053A5 (en) | 1976-10-06 | 1977-10-04 | METHOD FOR PRODUCING A MIXTURE FROM M-ARYLOXYBENZYL CHLORIDE AND M-ARYLOXYBENZALCHLORIDE. |
| BE181444A BE859358A (en) | 1976-10-06 | 1977-10-04 | META-ARYLOXYTOLUENE CHLORINATION PROCESS |
| JP11871577A JPS5346929A (en) | 1976-10-06 | 1977-10-04 | Process for preparing a mixture of metaaaryloxybenzyl chloride and metaaaryloxybenzyl chloride |
| NLAANVRAGE7710837,A NL188571C (en) | 1976-10-06 | 1977-10-04 | CHLORATION METHOD. |
| IT28272/77A IT1143702B (en) | 1976-10-06 | 1977-10-04 | PROCESS FOR THE PREPARATION OF A M-ARYOXYBENZYL CHLORIDE AND A M-ARYLOXYBENZAL CHLORIDE MIXTURE BY CHLORING AN M-ARYLOXYLENE, AND PRODUCT SO OBTAINED |
| FR7729768A FR2367039A1 (en) | 1976-10-06 | 1977-10-04 | META-ARYLOXYTOLUENE CHLORINATION PROCESS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB41526/76A GB1588517A (en) | 1976-10-06 | 1976-10-06 | Preparation of m-aryloxybenzyl chloride and m-aryloxybenzal chloride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1588517A true GB1588517A (en) | 1981-04-23 |
Family
ID=10420094
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB41526/76A Expired GB1588517A (en) | 1976-10-06 | 1976-10-06 | Preparation of m-aryloxybenzyl chloride and m-aryloxybenzal chloride |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4146737A (en) |
| JP (1) | JPS5346929A (en) |
| BE (1) | BE859358A (en) |
| BR (1) | BR7706612A (en) |
| CA (1) | CA1104159A (en) |
| CH (1) | CH630053A5 (en) |
| DE (1) | DE2744603C2 (en) |
| FR (1) | FR2367039A1 (en) |
| GB (1) | GB1588517A (en) |
| IT (1) | IT1143702B (en) |
| MX (1) | MX5162E (en) |
| NL (1) | NL188571C (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2383153A1 (en) * | 1977-03-09 | 1978-10-06 | Roussel Uclaf | NEW BENZYLIDENE HALOGENIDES, METHOD OF PREPARATION AND APPLICATION TO THE PREPARATION OF METAPHENOXY BENZALDEHYDE |
| US4377713A (en) * | 1977-09-26 | 1983-03-22 | Ethyl Corporation | Chemical process for preparing 3-phenoxybenzyl chloride |
| US4250340A (en) * | 1977-12-22 | 1981-02-10 | Croda Synthetic Chemicals Limited | Process for preparing aralkyl halides |
| US4399075A (en) * | 1981-06-25 | 1983-08-16 | Asahi Chemical Company, Limited | Process for producing chlorinated phenoxytoluene derivatives |
| CN107162880A (en) * | 2017-06-14 | 2017-09-15 | 山西千岫制药有限公司 | A kind of preparation method of 4 methoxyl group benzyl chloride |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2302228A (en) * | 1940-04-02 | 1942-11-17 | Du Pont | Method of chlorination with sulphuryl chloride and production of monochloro-trimethyl acetic acid |
| US3920757A (en) * | 1971-08-25 | 1975-11-18 | Dow Chemical Co | Chlorination with sulfuryl chloride |
-
1976
- 1976-10-06 GB GB41526/76A patent/GB1588517A/en not_active Expired
-
1977
- 1977-08-31 CA CA285,840A patent/CA1104159A/en not_active Expired
- 1977-09-26 US US05/836,807 patent/US4146737A/en not_active Expired - Lifetime
- 1977-10-04 DE DE2744603A patent/DE2744603C2/en not_active Expired
- 1977-10-04 BR BR7706612A patent/BR7706612A/en unknown
- 1977-10-04 FR FR7729768A patent/FR2367039A1/en active Granted
- 1977-10-04 NL NLAANVRAGE7710837,A patent/NL188571C/en not_active IP Right Cessation
- 1977-10-04 JP JP11871577A patent/JPS5346929A/en active Granted
- 1977-10-04 MX MX776450U patent/MX5162E/en unknown
- 1977-10-04 IT IT28272/77A patent/IT1143702B/en active
- 1977-10-04 CH CH1213377A patent/CH630053A5/en not_active IP Right Cessation
- 1977-10-04 BE BE181444A patent/BE859358A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IT1143702B (en) | 1986-10-22 |
| US4146737A (en) | 1979-03-27 |
| CA1104159A (en) | 1981-06-30 |
| NL188571B (en) | 1992-03-02 |
| NL7710837A (en) | 1978-04-10 |
| JPS5346929A (en) | 1978-04-27 |
| BE859358A (en) | 1978-04-04 |
| NL188571C (en) | 1992-08-03 |
| CH630053A5 (en) | 1982-05-28 |
| DE2744603C2 (en) | 1986-11-13 |
| JPS618809B2 (en) | 1986-03-18 |
| BR7706612A (en) | 1978-06-06 |
| FR2367039A1 (en) | 1978-05-05 |
| DE2744603A1 (en) | 1978-04-13 |
| MX5162E (en) | 1983-04-14 |
| FR2367039B1 (en) | 1980-01-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19971003 |